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Showing NP-Card for (2E)-Piperamide-C5:1 (NP0049244)

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Record Information
Version2.0
Created at2022-03-17 21:09:23 UTC
Updated at2022-03-17 21:09:23 UTC
NP-MRD IDNP0049244
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2E)-Piperamide-C5:1
Description(2E)-Piperamide-C5:1, Also known as piperamide-C5:1 (2E), belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms (2E)-Piperamide-C5:1 Is a moderately basic compound (based on its pKa). Outside of the human body, (2E)-Piperamide-C5:1 Has been detected, but not quantified in, herbs and spices and pepper (spice). (2E)-Piperamide-C5:1 is found in Piper arboreum, Piper hispidum and Piper nigrum. This could make (2E)-piperamide-C5:1 A potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049244 ((2E)-Piperamide-C5:1)


  Mrv0541 05061310412D          

 20 22  0  0  0  0            999 V2000
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4388   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2638   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1838   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5187   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  8  7  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
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 19 14  1  0  0  0  0
 20 12  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
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3D MOL for NP0049244 ((2E)-Piperamide-C5:1)

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3D SDF for NP0049244 ((2E)-Piperamide-C5:1)

  Mrv0541 05061310412D          

 20 22  0  0  0  0            999 V2000
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4388   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2638   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1838   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5187   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5658   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  8  7  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  8  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  2  0  0  0  0
 16  6  1  0  0  0  0
 17  9  1  0  0  0  0
 17 10  1  0  0  0  0
 17 16  1  0  0  0  0
 18 16  2  0  0  0  0
 19 12  1  0  0  0  0
 19 14  1  0  0  0  0
 20 12  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049244

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C(\C=C\CCC1=CC2=C(OCO2)C=C1)N1CCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO3/c18-16(17-9-3-4-10-17)6-2-1-5-13-7-8-14-15(11-13)20-12-19-14/h2,6-8,11H,1,3-5,9-10,12H2/b6-2+

> <INCHI_KEY>
XZTCTKKANUDQCW-QHHAFSJGSA-N

> <FORMULA>
C16H19NO3

> <MOLECULAR_WEIGHT>
273.327

> <EXACT_MASS>
273.136493479

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.488297193963177

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)pent-2-en-1-one

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
2.6119640420000008

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.1708893930870286

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
77.1854

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)pent-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0049244 ((2E)-Piperamide-C5:1)
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PDB for NP0049244 ((2E)-Piperamide-C5:1)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.122   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.455  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.019  -6.990   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.559  -6.990   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.543  -5.525   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.035  -5.525   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.789  -3.080   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      12.789  -4.620   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      14.123  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3    4    9                                                       
CONECT    4    3   10                                                       
CONECT    5    1   13                                                       
CONECT    6    2   16                                                       
CONECT    7    8   13                                                       
CONECT    8    7   14                                                       
CONECT    9    3   17                                                       
CONECT   10    4   17                                                       
CONECT   11   13   15                                                       
CONECT   12   19   20                                                       
CONECT   13    5    7   11                                                  
CONECT   14    8   15   19                                                  
CONECT   15   11   14   20                                                  
CONECT   16    6   17   18                                                  
CONECT   17    9   10   16                                                  
CONECT   18   16                                                            
CONECT   19   12   14                                                       
CONECT   20   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

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3D PDB for NP0049244 ((2E)-Piperamide-C5:1)
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SMILES for NP0049244 ((2E)-Piperamide-C5:1)
O=C(\C=C\CCC1=CC2=C(OCO2)C=C1)N1CCCC1
Download
INCHI for NP0049244 ((2E)-Piperamide-C5:1)
InChI=1S/C16H19NO3/c18-16(17-9-3-4-10-17)6-2-1-5-13-7-8-14-15(11-13)20-12-19-14/h2,6-8,11H,1,3-5,9-10,12H2/b6-2+
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Synonyms
ValueSource
Piperamide-C5:1 (2E)HMDB
Chemical FormulaC16H19NO3
Average Mass273.3270 Da
Monoisotopic Mass273.13649 Da
IUPAC Name(2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)pent-2-en-1-one
Traditional Name(2E)-5-(2H-1,3-benzodioxol-5-yl)-1-(pyrrolidin-1-yl)pent-2-en-1-one
CAS Registry Number117137-65-2
SMILES
O=C(\C=C\CCC1=CC2=C(OCO2)C=C1)N1CCCC1
InChI Identifier
InChI=1S/C16H19NO3/c18-16(17-9-3-4-10-17)6-2-1-5-13-7-8-14-15(11-13)20-12-19-14/h2,6-8,11H,1,3-5,9-10,12H2/b6-2+
InChI KeyXZTCTKKANUDQCW-QHHAFSJGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Piper arboreumLOTUS Database
Piper hispidumLOTUS Database
Piper nigrumLOTUS Database
Piper nigrum L.FooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzodioxoles  
Sub ClassNot Available
Direct ParentBenzodioxoles  
Alternative Parents
Substituents
  • Benzodioxole
    • 

  • N-acylpyrrolidine
    • 

  • Benzenoid
    • 

  • Pyrrolidine
    • 

  • Tertiary carboxylic acid amide
    • 

  • Carboxamide group
    • 

  • Azacycle
    • 

  • Carboxylic acid derivative
    • 

  • Acetal
    • 

  • Oxacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.08ALOGPS
logP2.61ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)2.17ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area38.77 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity77.19 m³·mol⁻¹ChemAxon
Polarizability30.49 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038834  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB018269  
KNApSAcK IDNot Available
Chemspider ID10192700  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12073743  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available